Sodium hydride → 1-(2-Nitro-2-methylpropoxy)-2,2,5,5-tetramethylcyclopentane

HRID 1731678

反応式

HRID 1731678 の反応式
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9].[H-].[Na+].[CH2:13]1OCCOCCOCCOCCOCCOC1.[N+:31]([C:34]([CH3:36])=[CH2:35])([O-:33])=[O:32]>C(#N)C.O1CCCC1>[N+:31]([C:34]([CH3:13])([CH3:36])[CH2:35][O:9][CH:3]1[C:4]([CH3:8])([CH3:7])[CH2:5][CH2:6][C:2]1([CH3:10])[CH3:1])([O-:33])=[O:32]

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 784862-Nitro-1-propeneHCID 5516962,2,5,5-Tetramethylcyclopentan-1-ol

生成物 1

HCID 201657161-(2-Nitro-2-methylpropoxy)-2,2,5,5-tetramethylcyclopentane

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2,2,5,5-Tetramethyl-1-cyclopentanol is added to a dry flask under argon at 0° C. Dry tetrahydrofuran was added with a syringe. Sodium hydride (60% dispersion in oil) is added quickly in one portion and the contents of the flask are stirred for one hour at room temperature. A 10 mM solution of 18-crown-6-ether in acetonitrile is added with a syringe and the flask cooled to 0° C. A tetrahydrofuran solution of 2-nitropropene is added with vigorous stirring over a 10 minute period. After completion of the reaction, as judged by thin layer chromatography, it is quenched with dimethyl sulfate, poured into saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield 1-(2-nitro-2-methylpropoxy)-2,2,5,5-tetramethylcyclopentane.

後処理

  1. temperaturethe flask cooled to 0° C
  2. stirringwith vigorous stirring over a 10 minute period
  3. customAfter completion of the reaction
  4. customis quenched with dimethyl sulfate
  5. additionpoured into saturated ammonium chloride
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer is dried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-e84bec7482c84afd98e0f2d59b817124
出典データセット
uspto-grants-1986_11
特許番号
US04622418

関連ノート

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